Equilibrium constants for the interconversion of substituted 1-phenylethyl alcohols and ethers. A measurement of intramolecular electrostatic interactions

ME Rothenberg, JP Richard…

Index: Rothenberg, Marc E.; Richard, John P.; Jencks, William P. Journal of the American Chemical Society, 1985 , vol. 107, # 5 p. 1340 - 1346

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Citation Number: 18

Abstract

Abstract: Equilibrium constants for the reactions of ring-substituted 1-phenylethyl alcohols with a series of aliphatic alcohols of pKa 12.4-16 to form the corresponding ethers, and for interconversion of the ethers, have been determined in 50: 45: 5 HOH/CF3CH20H/ROH (v/v/v), p= 0.5 (NaCIO,), at 25 'C. Formation of ethers from the alcohols is favorable, with values of K= 3-74; replacement of water by methanol is favored by factors of 50-74. ...

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